roadmap

Sync ROADMAP.md with GitHub Issues and milestones.

3|Updated Mar 18, 2026

Search Tags:#planning #github #roadmap #prioritization #milestones #issues

Ready to run

npx skills add https://github.com/rshade/agent-skills --skill roadmap-rshade

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: roadmap
Source: https://github.com/rshade/agent-skills/tree/main/skills/roadmap
Command: npx skills add https://github.com/rshade/agent-skills --skill roadmap-rshade

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Strategic roadmap management requires aligning ROADMAP.md with live GitHub data (issues and milestones). This Skill automates the synchronization, bootstraps planning docs from scratch, and provides concise status summaries to keep teams aligned.

Core Features & Use Cases

Sync ROADMAP.md with GitHub Issues and milestones to reflect current work.
Bootstrap CONTEXT.md and ROADMAP.md content for new projects or after major changes.
Brainstorm mode with boundary checks to surface ideas without committing changes.
Quick status summaries to highlight progress, gaps, and risks.

Quick Start

Run the roadmap synchronization workflow to align ROADMAP.md with live GitHub data.

Frequently Asked Questions about roadmap

High-intent search queries and answers about installing and using this skill.

FAQPage Schema

How do I sync a ROADMAP.md file with GitHub issues and milestones?▼

To sync a ROADMAP.md file with GitHub issues and milestones, you can automate the synchronization process to align your roadmap with live GitHub data. This updates your planning docs to reflect current work and milestone progress.

What is the best way to bootstrap planning docs for a new GitHub repository?▼

The best way to bootstrap planning docs is to generate CONTEXT.md and ROADMAP.md content from scratch. This creates the foundational roadmap files needed to align with GitHub issues and milestones for new projects.

Do I need GitHub CLI authentication to manage project roadmaps?▼

Yes, you need GitHub CLI authentication to manage project roadmaps. The roadmap synchronization uses the CLI to access GitHub Issues and milestones data required for aligning your ROADMAP.md with current repository activity.

Can I brainstorm roadmap ideas without committing changes to GitHub issues?▼

Yes, you can brainstorm roadmap ideas without committing changes using a dedicated brainstorm mode. This mode runs sessions with boundary checking against CONTEXT.md to surface ideas safely without altering live GitHub issues.

How do I get quick status summaries for GitHub milestones?▼

You can get quick status summaries for GitHub milestones by running a synchronization workflow. This highlights progress, gaps, and risks by reading live issues and milestone data from your repository to keep teams aligned.

Why should I enforce CONTEXT.md boundaries during roadmap synchronization?▼

You should enforce CONTEXT.md boundaries during roadmap synchronization to maintain project scope. This ensures generated ROADMAP.md content and brainstormed ideas stay within defined limits without overriding original project constraints.